Chloroform → HCID 59279643, compound

Participants

Reaction Steps

To a stirred solution of (4,6-dimethyl-pyridin-3-ylmethyl)-(2-fluoro-9H-purin-6-yl)-amine (0.6 g, 1.9 mmol) in DMF (10 ml) under an argon atmosphere, at RT, was added K2CO3 (powdered, anhydrous, 1.77 g, 5 eq, 13 mmol) followed by 2-bromopropane (1.8 ml, 10 eq, 19 mmol). The reaction mixture was stirred at RT for 24 h, when TLC (CHCl3:MeOH; 90:10) indicated that the reaction had gone to completion. The solvent was evaporated in vacuo and the residue partitioned between water (50 ml) and ethyl acetate (50 ml), the aqueous phase was separated and extracted with more EtOAc (2×50 ml). The bulked organic phase was washed with brine (50 ml), dried (MgSO4) and evaporated in vacuo, and the residue was purified by gradient column chromatography on silica gel, eluted with CHCl3:MeOH (100:0→95:5), to provide the product as a yellow film (0.4 g, 59%). δH (250 MHz, CDCl3) 1.52 [6 H, d, J 7.5 CH(CH3)2] 2.27 (3H, s, CH3), 2.45 (3 H, s, CH3), 4.73-4.62 (3H, m, NHCH2 and CH[CH3]2), 6.91 (1 H, s, ArH), 7.12 (1 H, NH), 7.47 (1 H, s, ArH), 8.32 (1 H, s, ArH); δC (250 MHz, CDCl3) 160.77 (C), 157.89 (C), 157.43 (C), 156.12 (C), 155.79 (C), 149.14 (CH), 137.7 (CH), 128.7 (C), 129.76 (C), 124.83 (CH), 47.2 (CH), 40.14 (CH2), 23.9 (CH3), 22.47 (2×CH3), 18.54 (CH3); m/z 315.3 (M+H)

Provenance & Evidence